Hydrazine hydrate (1:1) → HCID 22806755, compound

Participants

Reaction Steps

Compound 8 (1 g) was dissolved in 85% hydrazine hydrate (4 ml) and allowed to stand for 4 h at ambient temperature. The reaction mixture was diluted with 95% ethanol (20 ml) and the solvents evaporated. The residue was dissolved in 10 ml water and dialyzed against 5 changes of water in an ultrafiltration cell. Lyophilization of the water gave 8-hydrazinocarbonyloctyl 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (14) in quantitative yield as an amorphous solid, [α]D --72.8° (c 1.0, water). This compound and the 5-hydrazinocarbonylpentyl analog were used to prepare the following Lewis-a antigens [Lea -O(CH2)8CONH]n -BSA where n can have any of the following values 11, 22, 30, or 45; [Lea -O(CH2)8CONH]28 -HSA; [Lea -O(CH2)8CONH]15 -polylysine; [Lea -O(CH2)8CONH(CH2)2NH]10 -dextran; [Lea -O(CH2)5CONH]n -BSA where n was 10 or 30; [Lea -O(CH2)5CONH]25 -HSA by the acyl azide method (cf example XII). The abbreviation Lea as used above stands for the Lewis-a trisaccharide determinant: ##STR12## Goat antiserum prepared against the natural Lewis-a blood group substance was found to form a precipitate with the above Lea antigens.

Provenance & Evidence